US 7,419,978 B2
Phenyl-aniline substituted bicyclic compounds useful as kinase inhibitors
Jagabandhu Das, Mercerville, N.J. (US); John Hynes, Washington Crossing, Pa. (US); Katerina Leftheris, Skillman, N.J. (US); Shuqun Lin, Newtown, Pa. (US); Stephen T. Wrobleski, Whitehouse Station, N.J. (US); and Hong Wu, New Hope, Pa. (US)
Assigned to Bristol-Myers Squibb Company, Princeton, N.J. (US)
Filed on Oct. 21, 2004, as Appl. No. 10/970,420.
Claims priority of provisional application 60/513285, filed on Oct. 22, 2003.
Prior Publication US 2005/0143398 A1, Jun. 30, 2005
Int. Cl. C07D 487/04 (2006.01); C07D 487/14 (2006.01); A61K 31/53 (2006.01); A61P 19/02 (2006.01); A61P 19/10 (2006.01)
U.S. Cl. 514—243  [544/184] 10 Claims
 
1. A compound having the formula (I)

OG Complex Work Unit Drawing
a pharmaceutically-acceptable salt thereof, or an enantiomer thereof, or a diastereomer thereof, wherein:
K is nitrogen;
Z is selected from —NHR11, —C(═O)NR11R12, —NR11C(O)2R12, —NR11C(═O)R13, —NR11C(═O)NR12R13, —NR11SO2R14, —SO2NR12, —C(═O)R12, —OC(═O)R15, —C(═O)NR11C(═O)R13, —C(═O)NR11C(═O)NR12R13, and optionally-substituted heteroaryl;
R5 is hydrogen or C1-4alkyl;
R6a and R6b are
each independently selected from the group consisting of hydrogen, C1-4alkyl, hydroxy, methoxy, halogen, cyano, amino, —NH(C1-4alkyl), —N(C1-4alkyl)2, —CF3, —OCF3, and C1-4alkyl substituted with one or two of hydroxy, methoxy, halogen, cyano, amino, —NH(C1-4alkyl), —N(C1-4alkyl)2—CF3, and/or —OCF3;
R is independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, hydroxy, alkoxy, halogen, cyano, amino, alkylamino, haloalkoxy, cycloalkyl, aryl, heterocyclo, and heteroaryl;
R1 and R2 are taken together with the nitrogen to which R1 is attached to form a ring fused to ring D and the ring fused to ring D is selected from the group consisting of:

OG Complex Work Unit Drawing
R3 is selected from the group consisting hydrogen, methyl, perfluoromethyl, methoxy, halogen, cyano, NH2, or NH(CH3);
R9 is selected from hydrogen, alkyl, substituted alkyl, halogen, cyano, aryl, heteroaryl, —SR10, and —S(O)2R10, wherein R10 is alkyl or substituted alkyl;
R11 is hydrogen, alkyl, or substituted alkyl;
R12, R13 and R14 are independently selected from hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, hydroxy, alkoxy, aryl, cycloalkyl, heteroaryl, and heterocyclo, except R14 is not hydrogen; and
R15 is selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, cycloalkyl, heterocyclo, and heteroaryl.